Unrequited Love
by missdarcy7
Summary: Elena, an aspiring actress is forced to drop her life in LA to move to NYC for 3 weeks for a job she has been waiting her whole life for. Damon, the heir to the multi- billion empire Salvatore Hotels, a bachelor from New York City. Both from different backgrounds and lifestyles, they still manage to become best friends. But will they take their friendship to the next level?
1. Chapter 1

_**Los Angeles, CA - Elena**_

"And that's a wrap. We're done guys, great job everyone you all should be very proud of yourselves." Andy, my director of the last movie I made, said as he went around the cast and crew giving each and every one of us high- fives and a pat on the back.

I am not quite a big fan of this movie, I only did it because I knew it would be a summer blockbuster and that it would pay well, so I was glad that filming finally wrapped up after 4 long months. 2 weeks ago, my manager called me and said that Paramount wants to remake _Breakfast at Tiffany's,_ apparently the producers hand- picked 5 actresses whom they thought looked similar to the late Audrey Hepburn and that we were potential candidates to play the iconic role of Holly Golightly. Initially, I wanted to take a 3- month vacation with my boyfriend, Matt, who also is an actor; but after hearing about this potential career- changing opportunity I had to postpone all plans of going to Bora Bora and flew to New York City for a day for the audition. Matt, being the supportive and loving boyfriend he is, with it and even flew over to New York for moral support. The only down side to this job would be the fact that the production is set to shoot in New York City for 3 months, Matt unfortunately can't afford to stay in New York City with me as he needs to be in LA for pilot season auditions. Matt and I have not gone over 2 weeks without seeing each other so 3 months will be a very long stretch, and I don't think neither one of us are ready for that.

*Ring**Ring* "Hello Elena."

"Hey Steph, what's up?"

"I have bad news and good news, which one do you want first?"

"I don't like the sound of this give me the good news first."

"Okay, the good news is that I just got a call from the producers of _Breakfast at Tiffany's_ and you got the part!"

"Oh my god are you serious, this is the best news ever Steph, I can't believe it!"

"They said they found the right Holly once they saw you. I know how much this means to you Elena, I'm so proud. But, like I said I still have the bad news."

"Tell me the bad news then."

"They want you to fly to New York on Friday for the chemistry test and then start shooting the next week, which means…"

"Friday? That's tomorrow! I don't even get to say goodbye to Matt."

"Yes I'm sorry Elena, if you can't make it then they said they will find another actress, their schedule is really tight and everything must not be delayed."

"Ugh, fine I guess I have to go then, tell them I'm in."

"Perfect, you are on the next flight to JFK and you'll be leaving at 11pm tonight, Ben will be picking you up to go to LAX. Have a safe trip and trust me this will be very worth it."

"Thanks Steph, again for everything."

"Of course Elena, talk to you soon when you get to New York."

"Talk to you soon, bye."

I finally got home from work, all I wanted to do was to lie in bed and watch Netflix and snuggle with my dog Beau, but that's not going to happen because my flight for New York leaves in 5 hours. Matt and I have made an agreement that whenever we are not together we try out best to FaceTime each other every day. He is currently in San Diego visiting his dad who is battling lung cancer and just had a operation. Being the good son that he is, he drove up immediately and stayed by his side and Rob, his dad, was set to be released from the hospital. I dreaded telling him that I got the part, as I know that he would drive back down to LA just to say goodbye to me, but I really don't want to deprive him from spending time with his father. Immediately after I got off the phone with Steph, I called my mom to share with her the good news and my best friend Caroline.

*Ring**Ring* "Hey babe you look so tired, what's wrong?"

"Nothing it's just been a long day and I have something to tell you."

"What? Are you pregnant?"

"What? No no no, it's not that, I got the role of Holly!"

"Oh my god babe I'm so proud of you!"

"Thanks babe, but there's a down side to this, I'm leaving for New York tonight. My flight leaves at 11 tonight."

"What? You are leaving tonight?"

"Yea, they want me there tomorrow for the chemistry test and shooting starts Monday next week."

"Hey that's fine, good news is my dad is set to be released tomorrow morning, so I can fly up on Saturday to New York and stay with you until Monday morning and fly back to LA."

"Really babe, you don't have to, I know how tired you have been the last couple of days. You sure?"

"I'm sure, I'd do anything to see you, even if it's just for a day."

"You're the best, this is why I love you so much. I miss you."

"I miss you too. I'll see you soon though."

"I know I can't wait, I'll have a surprise for you."

"Love you."

"Love you too, gotta go now, I need to start packing for New York."

"Love you bye." With that, I closed my laptop and headed back towards my room to finish packing. It was November and the weather in New York is not like in LA where basically the only difference in the four seasons is hot and hotter. It was about to snow in New York in about 2 weeks time and I had to pack all of my winter clothes which took up more space than I had planned. I was done packing much faster than anticipated, before I left I had to drop by Caroline to hand over Beau for her to take care of him while I'm in New York for 3 weeks.

"Hey Care, are you ready for me to come over."

"Yea, I'm ready you can come over now."

"Okay perfect, I'll come over in about 15 minutes."

"Okay see you."

Caroline has been really busy with her life lately, after her TV show wrapped up in Vancouver she decided to move back to Los Angeles to further pursuit her film career here. She just moved into her new house in West Hollywood a week ago and her furnitures have just been placed properly today, so I had to call in in advance to check if she was ready for me, because normally I would just go over without notice. She also has been really lonely ever since she broke up with her on and off- screen boyfriend Tyler Lockwood and so I thought giving her Beau would help her get over her heartbreak a little more easier.

*Ding Dong* Caroline immediately opens the door after the first bell, "Welcome!"

"Oh my gosh Care, your place is so nice, I'm starting to get a little jealous, maybe I will steal some of your ideas for my place." I said as I nudged her.

"Wait till you see the kitchen, you will die. Beau! My cutie pie!" Caroline squeaked as she grabbed Beau off my hands into hers.

"Shut up, your kitchen will make Martha Stewart drool. I'll definitely come here more often than you would like me to." I joked. I could see from Caroline's face that she too, wasn't so happy about the idea that her best friend would be spending 3 weeks away her. Before I got offered the job, I was going to show Caroline around LA, introduce her to my group of friends in LA, have fun, catch up on life. But now that I'm about to leave for New York in 3 hours, things have shifted a great deal, I will be missing her house warming party, our other friend Bonnie's 27th birthday party and other things.

"Hey Care, it will be fine, I'll try my best to come home every weekend and as often as I can." I tried to comfort her as I went over to her for a hug, something which we both needed, support from each other.

'I know, it's just with the breakup and everything that's been going on right now, sometimes all I need is my best friend by my side. Don't get me wrong though, you are not going to stay here in LA because of me, you are going to get on that flight to JFK and you're going to stay in New York and be the best you can be on set, I'll believe in you Elena Gilbert, you're going to do great things."

I was so touched by what Caroline had said, I couldn't bring myself to words and simply gave her other bear hug.

"So what does Matt have to say about all of this?"

"He has been really supportive throughout this entire process and I couldn't ask for anymore from him. He can't stay in New York for 3 weeks straight with me because of pilot season auditions here in LA, and he is in San Diego with his dad right now. Thank God is feeling a bit better and will be leaving the hospital tomorrow morning and so Matt is driving back down to LA and his flight for JFK is Saturday morning and he is staying with me in NY for the weekend coming back to LA on Monday morning. So it's going to be really hectic."

"Oh wow, I really shouldn't keep you here for too long, you have a flight to catch missy."

"I know I know, here I brought Beau's food for 3 weeks and his vet's emergency no. in case any thing were to happen. Call me if you need anything and you know if you really need me I will be on the next flight back to LA in a heartbeat."

"I know and that's why you are my best friend. Love you, I'll miss you so much Elena."

"Love you too Care."

Ben came over to my house to pick me up right on time at 9:00 sharp. I was all ready to leave with my two filled luggages and a carry on, made sure I turned off all the switches, before I locked the doors of my house.

"You ready to leave Miss Gilbert." Ben said as he carried my luggages to the trunk of the car.

"Yes I guess so."


	2. Chapter 2

_**New York, NY - Elena**_

"Welcome to New York Miss Gilbert." I was greeted by a sign with my name written in sharpie by the assistant of one of the producers, Stefan and her name was Mindy.

"Thank you."

"Absolutely, Miss Gilbert. We have arranged for you to stay in an apartment in Midtown close to where we will be shooting. The apartment building is owned by one of our producers Stefan, so the entire cast and crew will be staying there during the production. We will now head straight to Mr. Salvatore's office for your chemistry test with Klaus, who plays George. He is British, and he is really cute, I reckon you both will have instance chemistry."

I blushed, "I hope so, I'm here to make the best movie I can. And please call me Elena."

"Okay Elena, now follow me to the town car."

We were driven by a chauffeur, navigating our way through NY's morning rush hour, finally, an hour later we arrived in front of the office building. During our car ride, Mindy gave me the excerpt from the script which Klaus and I had to reenact for the producers. I was on the phone the entire time, responding to work emails, and informing everyone back home that I made it to New York just fine and that I was off to my chemistry test. I texted Caroline and told her that my co- star was going to be Klaus Mikaelson and asked her if she knew of him. She quickly responded that she had a friend who worked alongside him and her remark was that he was extremely flirty towards everyone and was extremely attractive. Her exact words were, "Yea, he will make Matt extremely jealous." Great, I thought to myself, another problem I have to deal with. I texted Matt about him and told him that he has absolutely nothing to worry about. He responded, "Of course, I trust you enough in our relationship." That made me feel a bit more relieved.

We enter the building, I looked at the directory and saw 501-10 Salvatore Hotels Corp. 601-10 Salvatore Hotel Corp. 701-10 Salvatore Hotel Corp. I asked Mindy, "Are you sure we are at the right building, look, it says Salvatore Hotel Corps, aren't we supposed to go some sort of production company?"

"Like I mentioned before Mr. Stefan Salvatore, the producer who you will be auditioning for, his family owns Salvatore Hotel Corp. and a lot of New York City's most expensive real estate and the building that you will be staying in is also his family company's. So no you are wrong, we are at the right place. Now did you bring your ID card."

"Yes, hold on let me find it in my bag." I said as a rummaged through my messy carry- on bag filled with documents and contracts and my flight essentials. "Found it." I handed over my ID Card to the security at the front desk, it is a protocol for the security of the building to check everyone's ID to see if they have been registered to enter the building. We were then escorted by Salvatore Hotel Corp. employees up to the 7th floor where Mr. Stefan Salvatore would be waiting for my arrival. Their office was much more simplistic than I thought, everything was either in black or white, decor- wise. Mindy led my through the cubicles and we arrived before Stefan's office.

*Knock**Knock* "Yes, who is it."

"It's me Mindy, Mr. Salvatore, I have Elena Gilbert with me."

"Great, have her come in please." Mindy opened the door and motioned me to enter. I timidly walked towards Mr. Salvatore, "Nice to meet you Mr. Salvatore, I'm Elena." I said as I reached my arm out for a handshake.

"It's so good to finally meet you. I'm Stefan, and please call me Stefan." Hmm, Mr. Salvatore is not too shabby himself, I'm surprise he didn't opt to be in front of the camera.

"Klaus should be here any minute, he texted me and he said he is coming straight from SoulCycle so he should be here in about 5 minutes. In the meantime, tell me more about yourself, what have you been up to recently?"

"Well, I just wrapped up a summer movie which is set to premiere next summer which I am really excited about. At the same time I have been recording for Pixar's new animated movie Cars 2, which has been quite a nice change of scenery as I have never done a voice over before. So it's been quite a busy couple of months."

"Wow Elena, I'm impressed, it's true when they says you are one of the most hard- working up and coming stars. I just looked over your résumé and I have to say, you really are going to great things Miss Gilbert, they say your role in _Moonwalk_ is up for nomination for the Golden Globes."

"Thank you sir, that's really nice for you to say. I'm also-" Before I could finish my sentence, we were interrupted by a knock on the door.

"Who is it? Come in." We were both expecting it to be Klaus but when he started speaking without the British accent I knew it wasn't him.

"Stefan, I need you to confirm right now if you can come to Turks and Caicos for the grand opening 5 months from now."

"Yea, _Breakfast at Tiffany's_ will be done with production by then, so yea I should make it, and plus I won't miss an opportunity to Turks and Caicos are you kidding me?"

"Right, brother, okay I will tell Dad you are coming." If I thought Stefan was cute, this guy was every girl's fantasy. He was dark, tall and handsome, had the bluest eyes that could compete with the waters of Maldives, his hair was at perfect length with the correct shade of black, he was well- dressed in a slim fit suit, probably custom made and not to mention he had just the right amount of scruff on his chiseled jaws. He was perfect. Crap, I can't fantasize another man, I am happily in a relationship with matt. But my god was he absolutely gorgeous.

He averted his eyes towards me, our eyes meet, he gave me a smirk, "Pardon my interruption, my name is Damon Salvatore by the way, I'm Stefan's older brother, and I'm also the CEO of the company."

"Hi, my name is Elena and I'm actually working for your brother for the next 3 months, nice to meet you" Before I reached my arm over for a friendly handshake, he lifted my hand gently and brought it up to his mouth for a kiss, "The pleasure is mine." I was a little thrown off by his ego and he seems a little too touchy feely for me, especially since I have a boyfriend, I'm not used to men greeting me with a kiss on my hand.

"Well, I will leave you two together, it was nice meeting you Elena and would you care to join us out tonight, I'm throwing Stefan a celebration party for producing _Breakfast at Tiffany's_ , and it would be great if you could join us."

"Sure I would love to."

"Sounds great, Stefan will give you the details for the location and time, won't you baby bro? So see you tonight then."

"See you."

"Well, your brother seems a little…"

"Cocky?"

"I wouldn't say cocky…"

"It's fine, you can say it he is extremely full of himself, but I love him because he is my older brother and I know he will always have my back."

"You two don't really look alike either."

"People say I take on my mother's side, and Damon is the exact replica of my father."

Klaus finally comes in, and we did our chemistry test together and it worked out perfectly. Everything went as planned and Stefan was happy with what we delivered. Stefan also invited him to come tonight to the party and apparently many important people from the industry will be there tonight so we had to be on our best behaviors, which means no more than 2 drinks for me. Klaus and I got along really well, he is such a charismatic guy and we both have mutual friends from the industry and we both love dogs. He informed me he is single and is looking for a relationship, I told him that my best friend is single as well, fresh out of a relationship and I think that they would look cute together. Being the gentleman he is, he kindly asked to see a photo of her, I showed him a picture of Caroline looking stunning in a Ellie Saab dress at this year's Emmy's and his initial reaction was, "Wow, she is a smoke bomb, she really is fit isn't she?"

"Yea, she is also a great person, she is beautiful inside and out. I'll hook you guys up when she comes to visit me in New York."

"Elena, if this works out, I will be in debt to you for life."

"Oh god Klaus, don't be silly."


	3. Chapter 3

_**New York, NY - Damon**_

I have never been more infatuated with other girl since Katherine. Elena, what a beautiful name, she exudes beauty from head to toe, absolutely flawless. Her silky brown hair, her perfect cheeks, her toned body, her mile- long legs, her tanned skin. I can go on and on about how stunning of a human being she is. I have to get to know her better, knowing Stefan, I'm sure he is drooling like a starving puppy around her and not sure how to make the next move. Elena is too good for Stefan, god she is probably too good for me. She seems like a sweet and lovely girl, way out of my league. I immediately went back to my office and googled Elena Gilbert, immediately thousands of google images came up of her at red carpet events, movie stills and paparazzi shots, apparently she is one of the biggest stars in Hollywood, in my eyes the only star, how haven't I seen one of her films? I must get started on a Elena Gilbert Marathon tonight after the party. The second thing that pops up on Google when one searches for Elena Gilbert, is Matt Donovan, who is her boyfriend, " _Elena Gilbert spotted kissing TV Star Matt Donovan at Lakers Game", "Elena Gilbert and Matt Donovan went out on a date at Craig's last night"._ Who is this Matt Donovan person? He looks like your typical American varsity football stud, he has blonde hair and isn't even that fit, I'm sorry but Elena has really bad taste. But hey, just because there is a goalie doesn't mean you can't score, and the midfielder is Damon Salvatore.

I'm really excited about tonight's party, A, because I organized it myself and I'm really happy with the end result; B, I'm honestly proud of my baby brother for pursuing something he is truly passionate about - film production; and C, I can't wait to see Elena again. Usually it takes me 10 minutes to get ready put on an outfit, but tonight I had to look extra suave, I had to dress to impress. I was feeling really classy tonight and so I decided on a Giorgio Armani suit with my classic Gucci loafers.

The party was supposed to start at 7:30 at the The Standard at the High Line, and around 50 people were to attend, not including their dates. With my connections, I managed to rally up quite a number of esteemed guests from the movie industry and so I am expected to be on my best behavior to save face for Stefan and the Salvatore name. I arrived early at 7 just to make sure everything was in order before everyone else arrived. I wasn't going to be early alone so I called up my best friend Alaric to come join me and he came without questions.

"What's up brother."

"Hey Alaric, thanks for coming man, you're the best."

"Free food and booze. I'll clean the floor if you want me to."

"Funny Saltzman."

"Salvatore why are you so dressed up tonight? Trying to impress someone."

"Actually yes I am."

"Damon Salvatore is dressed up to impress a girl?!" Even I couldn't believe it until Alaric said it.

"Once you see her, you'll understand." I said, trying to keep it cool.

"What's here name?"

"Elena, Elena Gilbert she is an actress. Do you know her by any chance?"

"Elena Gilbert, shut up she is my girlfriend's niece. Damon, you can't start anything with her, she is in a relationship."

"I know, still that doesn't mean I can't try."

"Damon, if you do anything that will hurt her, and that includes trying to get into her pants, I will beat the living crap out of you, she is my girlfriend's family and I will not hear the end of it if something happens."

"Jeez. Guess I'll have to find another wingman then."

"I'm telling you I don't approve of whatever you are trying to do. Don't play any of your games with her."

Alaric left me alone at the bar table for me to ponder on what he had just said. To come to think of it, maybe I shouldn't play one of my games with her, I honestly truly can see myself being in an actual relationship and I don't want to do anything to jeopardize that. It would be best for me to get her to like me as a friend and we'll move from there. This should be a piece of cake, I thought to myself.

People starting to arrive, the tall tables that were scattered sparsely along the patio were starting to be filled with guests socializing with drinks on one hand and hors d'oeuvres on the other. Stefan, the man of the hour finally arrived and everyone greeted him with a round of applause and cheering. I went over to him to congratulate him on his accomplishment and handed him a little gift I got him from Hermès. Afterwards, I walked around the patio, introducing myself to people I didn't know, thanking people for coming and making sure that everything went accordingly.

I scanned my eyes across the party, trying to find Elena to say hi. I wanted to seem subtle, so I pretended to roam around for a few minutes until I finally spotted her giggling away with Klaus Mikaelson who plays her opposite in the movie. Great that son of a gun is flirty with my girl. I walked over towards them, Elena caught me and waved.

"I'm sorry to interrupt once again, I'm so glad you made it Elena, it's so nice to see you."

"Thank you for inviting me, you're such a good brother for organizing this for Damon, you've done a wonderful job." She said as we gave each other double kisses on the cheek.

"It's the least I can do after all the hard work Stefan has done to start his own film production company. I'm very proud of him. I see that you don't have a drink with you, would you care for one?"

"Sure, I'll have a margarita please."

"Okay, hold on a second, I'll go get it for you."

"Here, I'll walk to the bar with you."

"Wow, this margarita is amazing."

"I'm glad you like it. Cheers." I lifted my glass of bourbon.

"Cheers."

"So how do you like New York City?"

"I love it, I love everything is open till late at night, you can always walk to places unlike in LA where your car is your pair of legs. It's true when they the city never sleeps. The food here is great too." Elena took another small sip of her margarita. I noticed I was watching her every move intently.

"What's your favorite cuisine?"

"Japanese. I love that sushi place here, Sushi of Gari, they have the best crispy spicy tuna roll, my boyfriend and I went there last time when we were here together."

"Love that place. Why isn't your boyfriend here in New York with you?"

"Well, he just got back to LA from San Diego. He's actually flying to New York to see me tomorrow morning and he's staying here for the weekend with me and he's gonna fly back on Monday. He has to stay in LA for work which is a bummer, but we will both make an effort to see each other on the weekends. Either Matt's gonna to fly to NY or I'll fly back to LA. We'll make it work, god I miss him already."

Hearing her talk about missing Matt made me feel for her, I could see in her eyes that she was really reluctant to leave her life behind in LA, it was almost as if she was forced to come here.

"Hey, it will work out just fine." I said and I patted her back, trying to comfort her.

"I literally just met you today, and you have been so nice to me, thank you so much."

"I'm a nice person, what can I say."

"To be honest with you, I thought you were super cocky when I first met you in Stefan's office this morning, so I wasn't expecting all this nice guy act."

"What? This is not a nice guy act, Elena." I caught a glance at Alaric and motioned him to come over by waving my drink,

"What are you doing Damon?"

"I'm going to introduce you to my best friend and he is going to vouch for me that I'm actually a nice guy."

"Alaric Saltzman!"

"Hey Damon, I just came over for a drink." "Scotch on the rocks please." Alaric said to the bartender.

"Alaric, meet my new friend, Elena, Elena meet my best friend Alaric."

"Elena it's so nice to finally meet you, I've heard a lot about you from my girlfriend, Jenna. I'm Alaric." Alaric said as he leaned in for double kisses on the cheek.

"Oh my god, it's the infamous Alaric Saltzman. For a second I was scared when you said you've heard a lot about me. Tell Jenna I said hi to her and the fam. I'm so glad I finally got a chance to meet you in person. Where's Jenna? Is she here."

"She's back in Mystic Falls, but she will be back in the city next week, so you guys can catch up when she's back."

"Definitely. This is such a small world."

"I know, I can't believe as well."

"It's getting late now, I think it's time for me to head out, I'll go say bye to Stefan first." With that, she left our small circle and headed over to say goodbye to Stefan, she had a small conversation with him and gave him a goodbye kiss on the cheek and walked over back to us.

"I'm back, so guess I'll see you guys soon."

"Hold on, how are you planning on getting back home?"

"I think probably by subway then I'll walk, why?"

"Uh ah, you are not going home by subway, I'll have my driver drive you home."

"You really don't have to Damon, I'm a big girl it's fine."

"No I insist Elena, New York City can be dangerous at night, and a pretty girl like you shouldn't be walking by herself alone on the streets."

"Okay fine if you insist then."

"Here I'll walk you out." I guided her through the crowd with my hand placed gently behind her back. My car pulled over right on time when we walked out of the lobby.

"It was so nice seeing you tonight, I hope you can see each other some time soon, I'll probably come on set to visit my brother, so sometime this week you'll get to see me."

"The party was great Damon, nice job and thank you so much again you really didn't have to do this you know. Bye." We gave each other a good bye hug and I made her promise me to text me when she arrives at the apartment building. She looked at me weird but said okay. Normally, I don't ever tell my girlfriends to text me when the get back, but with Elena, I needed to know, it was as if this protectiveness aroused in me all of a sudden.


	4. Chapter 4

_**SoHo, New York - Elena**_

Production began bright and early on Monday morning at 5 am. Klaus and I would work from 5-12 then again from 3-6, everyday besides the weekends until the 3 weeks was over. In the next few days, I began warming myself up to the rest of the cast and crew. Everyone around me seemed so nice and had good intentions for this production to be the best it can be. I was surprised to see Stefan on set pretty much the entire time, he is truly the hard working person Damon described him to be. Speaking of Damon, he texted me last night to ask me if he could come on set to see how it was going. I was quite weirded out by out, I mean he shouldn't have to ask me for permission, if anything shouldn't that text message be sent to his own brother. Whatever, so I told him of course and said why don't you drop by when I'm working at around 4.

"Cut. Guys we are taking a 5 minute break then we are going to wrap up Scene 2 for the day." Our director Mark is one of the best in the industry and the nicest guy I have ever met. He believes in the artists' expertise so much that he allows a bit of improvisation throughout the movie. I was done for the day as my character doesn't have any port in the rest of Scene 2. As I was walking back to my trailer, I bumped into Damon.

"Look who is here." I leaned forward and gave him a kiss on the cheek and a hug, "Hi Damon."

"Hey Elena, how is the production going?"

"So far so good and I'm actually also done for the day."

"Oh really, I was actually going to ask you, are you free tonight?"

"I mean, I was going to cuddle in bed and watch Netflix but what do you have in mind Damon?"

"Alaric, Jenna and I are going out for drinks tonight and I don't want to be awkwardly third- wheeling so would you like to accompany me please?

"Oh my gosh, Aunt Jenna didn't even tell me she was coming back to the city today."

"Yea, she is landing in an hour and Alaric is on his way to JFK."

"Great, sounds good."

"I'll wait for you in our lobby at 8 and we can go together."

"See you Damon," this time Damon initiated and leaned over and gave me a goodbye kiss on the cheek and a hug,

"Bye Elena."

It only struck me when Damon said "our lobby" that he was living in the same building as I am. I feel like such a bad person, every time I see Damon or talk to him I start to blush a little and get butterflies in my stomach; like a high school freshman talking to their senior crush.

The first thing I did when I got home was rummage through my limited closet to find a cute but not so revealing outfit for tonight. I found two potential outfits that I would choose but was faced with the hardest dilemma, which dress should I pick, should I go with the black dress with black heels, red dress with black heels, black dress with red heels, I could go on forever with the options. So I decided to call Caroline, who basically is like my personal stylist.

*Ring**Ring* Thank god she picked up in the first ring.

"Caroline! I need your help. Damon came by to set today and he invited me to drinks tonight with Alaric and Jenna, I have a problem, which outfit should I wear." I showed her the three options that I had.

"Woah whah whah, is this a double date? Elena Gilbert do I need to remind you that you have a lovely boyfriend waiting for you at home. And please wear the black body con with those black Manolos, they look to die for."

"Caroline, promise me you won't judge me, after this weekend with Matt, I just don't really feel any sparks with him, like we didn't even have sex or anything. But every single time I talk to Damon, I get butterflies in my stomach and act like a little girl."

"What? So are you saying that you might break up with Matt?"

"I don't know. I mean I would feel like such a bad person if I did it over the phone, I can't do that to him."

"Does Damon know about how you feel?"

"Of course not. I don't know but I think that Damon kinda of likes me already."

"Oh Elena, as your best friend, I think it's best for you and Matt to talk to each other and maybe even tell him how you actually feel."

"Ok Care, thanks for your advice, I gotta go now and start getting ready."

"Bye Elena, love you and take care."

"Love you Care."

It was already 6:30 and I had just about an hour to put my makeup on, and 20 minutes to straighten my hair and I still had to take a shower. As I was applying my concealer on, I got a text from Damon saying, "Hey just an FYI, the place we are going to have drinks is kinda of fancy schmancy." I quickly responded, "thanks for the heads up."

After 2 and a half hours of getting ready I was finally ready to take off. I went down to the lobby only to see Damon waiting for me, sitting on the couch on his phone. I walked in front of him and he still didn't realize I was in front of him, guess he was reading something extremely important on his phone.

"Hi Damon," Damon jumped a little of his seat and was startled to see me.

"I'm so sorry I was reading a contract for one of the new boutique hotels in LA. Hi Elena, you look beautiful."

"Thank you." I could feel myself blushing. He didn't look to shabby either, he was wearing a white fitted shirt that was so tight I could see the outline of his abs, and a nice jacket to top it all off, his hair was gelled back, he reminded me of Leo DiCaprio's Jay Gatsby.

"Shall we Miss Gilbert." He said, as he lifted his arms, waiting for my arm to complete the knot. We walked out together and the doorman hailed a cab for us.

On the taxi ride over, Damon and I sat awkwardly without saying a word. I felt really uncomfortable and so I began to text Caroline, pretending I was invested in some important conversion. While I was "pretending" to text Caroline, I received a text message from Matt that said, "Hey babe, how are you, are you free to FaceTime right now? Miss you." Crap, I totally forgot that we had planned over the weekend to FaceTime every other night. I guess Damon could sense that something was wrong and so he asked, "Elena why are you fidgeting, is there something wrong?" "No, everything is all good, Matt just texted me to see if I could FaceTime, but I clearly can't so." "Oh. Are you going to tell him that you are out with me." Is he really kidding or not. I turned to look at him with a "are you shitting me" look. "What do you think genius?" And with that we continued back to our original awkward state of not talking to each other.

After 10 long minutes we finally arrived to SoHo and I was able to breathe in some fresh air cause Damon's enormous ego sucked all the oxygen out of the cab. We walked into the dive bar together and saw Alaric and Jenna sitting right in the corner.

"Hey guys!" Alaric called out.

"Hi Aunt Jenna! It's so good to see you!"

"Same here Elena, it's been what 3 months since we last saw each other. Hi Damon, how are you?"

"Good, been quite busy at work but how about you yourself?"

"Oh you know, nothing much, per usual."

Damon asked, "What drinks do you guys want?"

"Gin and tonic." "Whiskey" "My usual. Thanks."

"Got it, coming right up."

"My usual huh, I'm assuming you have been hanging out with Damon more than you have with your boyfriend."

"Stop it Aunt Jenna,"

"I'm just saying, Elena, remember that you still have a boyfriend."

"I know, Damon and I are just friends, nothing more than that I swear."

"I don't think my boy Salvatore and you are on the same page, he has never hung out with the same girl twice, unless he is banging the girl."

"Ok Alaric, I didn't need to hear that."

"Sorry to make you feel uncomfortable, but my point is I think he likes you more than he should." Before I could even say anything, Damon came back with all our drinks.

"Thanks Damon." He took a seat next to me and put his arm across my seat.

"So tell me Elena, how is the movie going?"

"So far so good, I get along well with every one in the cast and crew, Mark, our director, is amazing so that's always a plus. Considering our tight budget, our production team is doing a superb job with what they have. Oh and Damon, I was so surprised, Stefan is truly one of the most hardworking people I know, he is on set from the beginning of the day till the end, props to him."

"I know, my little brother is really passionate about this project and really wants it to work out." Alaric and Damon began their boy talk on their fantasy football teams, Jenna had to take a call from her boss, and I got another text from Matt after I told him I won't be free to talk tonight, he said, "Where are you? Are you with someone?"

I stepped out of our table and went to the back of the restaurant to respond to Matt's text. I responded, "I am out with my cast for drinks tonight and won't be back home till later tonight, will try to FaceTime you this time tomorrow night. Love you." I guess Damon noticed that I left and came looking for me. Just when I looked up from my phone, I saw Damon right in my face.

"You scared me the living crap out of me Damon. Please don't ever do that again."

"I'm sorry I scared you, is everything ok?"

"Yes, everything is fine, I was just about to go back."

"By the way, Alaric, Jenna and I are planning to go out tonight, we were thinking of going to Pacha, wanna come?"

"Sure, why not."

 _I want you to breathe me, let me by your air, let me roam your body freely. No inhibition, no fear._

 _How deep is your love? Is it like the ocean? What devotion are you? How Deep is your love? Is it like nirvana? Hit me harder again. How deep is your love? How deep is your love? How deep is your love? Is it like the ocean? Pull me closer, again. How deep is your love?_

This song was my favorite Calvin Harris song. I quickly moved to the dance floor and started to dance by myself. At this point, I had three drinks already, I was sort of out of it. Before I knew it, I felt a man place his hands on my hips and I naturally started to grind on him. I didn't even care to turn to see who he was. In the middle of the song, I turned around to see that this man was some random guy, he held my hands and we started to dance, _so tell me how deep is your love, can we go deeper? So tell me how deep is your love, can we go deep?_ All of a sudden I felt his lips on my lips and we were full on making out. I quickly pushed him away, and proceeded to exit the dance floor. I was walking towards to bathroom only to be stopped by an intoxicated Damon.

"What were you doing with that man huh? You're mine Elena, goddamit, if I see that man ever again I will punch him in the face, how dare him touch my girl, my Elena."

I quickly regained consciousness after he said that, "Damon, I think you are really drunk, I think you should go home now." I grabbed his hand and tried to pull him towards the front entrance of the club, but his hand was so much more forceful than my pull. He grabbed my face and pressed his lips hard against mine and kissed me, I was so mesmerized by his kiss that I didn't stop him.

"Damn, I have been wanting to do that to you the minute I laid my eyes upon you." With that, he left me in awe of what had just happened.


	5. Chapter 5

_**New York, New York - Elena**_

"Hello,"

"Hi Matt, what's wrong?"

"Look Elena, I'm going to cut right to the chase, my friend Luke showed me some pictures on Instagram of you making out with two guys last Monday night when we were supposed to FaceTime, you lied to me."

"I'm so sorry Matt, I swear I was so drunk I didn't know what I was doing."

"Elena, this long distance thing isn't really working, I haven't spoken to you since I left New York besides a few text messages here and there."

"I'm so sorry, work has been taking up so much of my time and energy. I feel extremely bad for not being the good girlfriend you deserve, maybe we should take a break."

"Elena, do you even love me?"

"I do," I tried to hold my tears and sobs, " I think we should just break up, it's not working anymore. Honestly, when you came to visit me in New York, I didn't even feel sparks for you like I used to."

"Is this because of what's his face, your producer's brother, Dan or whatever his name is?"

"It's Damon and no it's not because of him. It's us, our relationship isn't healthy and the way it should be."

"Well good talk Elena, I'm done with you for life and for good. Please don't ever talk to me again, I will bring all of your stuff from my place to Caroline." With that, he hung up on me.

I began to sob uncontrollably, I knew at some point I was going to break up with Matt, but never in a million years did I imagine us ending our relationship like this, over a freaking phone call. In the meantime, I received 10 texts messages from Damon, asking me if I had plans tonight. I didn't have the energy to entertain him so I continued to let my phone vibrate. I decided to cheer myself up so I turned on the TV and _The Ugly Truth_ was on, perfect this was one of my favorite rom- com. I was so sad about my life and my failed relationship that I didn't even laugh or move when it was the vibrator scene in the restaurant. Then, my door bell rang. I was a bit surprised, I wasn't expecting anyone, I slowly walked over to my door and opened it to find Damon Salvatore. Of course.

"Hi Damon, what are you doing here?"

"I texted you 100 times asking if you wanted to do something with me because I am extremely bored and I have no one to spend my Friday night with. So please can I hang out with you tonight? We could watch a movie and order Thai takeout?"

"Thanks for the offer, but I am not really feeling like doing anything tonight."

"What's wrong? Your eyes are pretty swollen to say the least."

"Matt broke up with me over the phone just now. So I am not in the mood to do anything tonight."

"Can I come in then?" I wasn't going to argue with him so I let him come into my apartment.

"I'm so sorry my apartment is a bit messy, I haven't gotten the time to clean my shit up."

"It's fine." We sat on my couch, and I turned the TV off. I curled my knees up and wrapped my arms around my knees and sat facing him.

"You don't have to tell me anything if you don't feel comfortable."

"He called me a liar, his friend showed him photos of me making out with you and another random person last Monday night. I told him that our relationship isn't at a good place right now so I suggested for us to take a break and he straight up told me that we were over and that he doesn't ever want to talk to me again. Damon, I feel like such a shitty person right now." I began to sob, "I fucked up big time, I cheated on my boyfriend."

"Hey," Damon leaned in closer to me and wrapped his arms around me, I nestled into his shoulders and began to cry ever harder onto his gray sweater. "you are a good person Elena, always remember that."

"No I am not, he even said the reason why I don't feel sparks for him was because of you."

"Shh, don't cry babe," He said as he gently stroked my hair. I was still crying but I felt a sense of warmth and protection being wrapped around his arms.

"Elena, I'm hungry. Do you mind if I grab something to eat."

"Oh my god, I'm so sorry, I didn't even realize it was 9:30, you must be starving right now. Here I have some leftover lasagna from last night, I could heat it up for you right now."

"Sure, that's good for me." I stepped out of his embrace and walked slowly to my fridge and retrieved the cold lasagna out and placed it in the microwave. Damon followed me to the kitchen and sat on my kitchen bar, waiting hungrily for his dinner.

"I'm sorry for making your night miserable. God I suck as a person. First I ruined Matt's life now your Friday night."

"Elena, you did not ruin my Friday night, in fact, I was the one that come over to your place, I wanted to spend my Friday night with my favorite person." I turned around to look at him, "Wait, I am your favorite person?"

"Well I mean, besides Stefan, yes, you are my favorite person to spend time with. You are good company Elena Gilbert."

"Looks like the lasagna is done." I placed the lasagna onto an actual plate and served it to Damon, "here you go, do you want something to drink?"

"Beer please."

"Heineken or Budweiser?"

"Heineken please." I gave him his beer and sat across from him.

"So you heard about what happened to me, what's up with you Damon Salvatore?"

"Well, I'm single, been single for a while now actually as a matter of fact, I haven't slept with anyone in 2 weeks. Now that's a record for me."

"I'm sure it is. What else besides the fact that you are single and horny." I teased.

"Who said I was ever horny Miss Gilbert?" And we both just started bursting laughing, then we entered a silent pause. He stared intently into my eyes and I gazed into his deep blue eyes.

"I forgot to mention you look beautiful as always Elena."

"Thanks Damon but I'm not wearing an ounce of makeup right now."

"You are still gorgeous. Here let me clean my plate and afterwards we can go watch a movie."

"Sounds good, what do you want to watch? Comedy, drama, action, thriller?"

"Whatever you want."

 _ **Los Angeles, California - Damon**_

California, my second favorite state after the wondrous Empire State. I love going back to California to visit my friends from USC and plus the state is home to the hottest girls in the country. I was meeting up my best friend from college Noah who is bringing me to his friend and model Jenny Kenner's birthday party.

"Look who it is, Damon Salvatore, same old same old. How are you brother? I haven't seen you in forever!"

"Nothing much Livingston, it's so good to see you too brother."

"How's life going for you in the Big Apple? Are you even dating anyone right now or you are not about the relationship life."

"I mean there is this girl that I like, her name is Elena, but she doesn't really seem like she is into me and I haven't spoken to her in a week so I'm technically single and I am planning on having a good time tonight."

"Perfect, because the birthday girl texted me this morning asking me to bring some of my hot guys friends cause she really wants to hook up with someone. So you're welcome Salvatore, Jenny is also a total babe."

"I don't know if I want to do that."

"Trust me Damon, you will change your mind once you see her."

The entire Hollywood was at Jenny's party and not to mention all her girlfriends that she invited were smoking hot. The party was so crowded that Noah and I didn't even get a chance to tell the birthday girl "happy birthday".

"Noah, oh my god I'm so glad you made it and I see you brought your friend." She turned to me, "Hi I'm Jenny Kenner, what's your name?"

"I'm Damon Salvatore, nice to meet you and Happy birthday!" I leaned in and gave her a kiss on the cheek and a hug.

"Thank you."

"I'm going to leave you two together, Jenny, do you know where Bailey is?"

"Yea, I think she is with my sister and all of the crew over there."

"Ok thanks and have fun." Noah intentionally left us alone together but I wasn't going to complain because it was true when Noah said I was going to change my mind about hooking up with Jenny because this girl was stunning.

"You look gorgeous tonight birthday girl." I said as I reached over to tuck her hair behind her ear.

"Thanks. You don't look too bad yourself Damon. Hey, it's time for me to get the birthday cake want to go in front with me?"

"Sure." She grabbed my hand and navigated through the crowd until we got to the stage.

"EVERYBODY LISTEN UP. I WANT Y'ALL TO STOP WHAT YOU ARE DOING AND SING HAPPY BIRTHDAY TO THE JENNY WITH ME." Under the DJ's lead, the entire party, every single one of them, sang "Happy birthday" to Jenny in unison.

"HAPPY BIRTHDAY TO YOU! WOOHOO!" Jenny blew her candles and gave a toast to everyone and thanking them for coming to celebrate her 20th birthday with her.

''Well that was quick, want to go out to the balcony, I need some air."

"Yea sure."

Once we were seated we started to chat, "so what brings you here to LA? Are you a movie producer like Noah?"

"No, I'm a businessman and I live in New York City, I work for my dad and our company runs and owns hotels all around the world, so I am here in LA just to check out the site for our new boutique hotel that will open in 2 years."

"I love New York, I actually go there a lot for work."

"Noah said you are some sort of big shot model, didn't you walk for Victoria Secret?"

"Yea I did, it was so much fun."

"You know what Jenny, you're different."

"What do you mean? Is that a good thing?"

"Yes of course, you are different in the sense that you aren't like every other girl I have met in LA and even back at home in NY, you are actually genuine and it is quite a rarity these days."

"Thank you, I will take that as a compliment. Do you want to head back in?"

We were in the middle of the party, in the center of the dance floor. Not to brag but I have Latino blood in me so I can bust a few moves. Everyone around me was cheering me on for breaking it down. I was dancing with Jenny, and we were grinding on each other and having a good time and all of a sudden she grabbed my face and started to make out with me, at that moment I forgot about everything, I forgot about Elena and all I could think about was Jenny. I kissed her back even harder. "Do you want to come home with me?" she whispered into my ears, "Gladly."


End file.
